4-Nitrophenol → 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 2372998

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HRID 2372998 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@@H:6]1Br)(=[O:3])[CH3:2].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(Cl)Cl.CCOCC.[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:29][C:26]1[CH:27]=[CH:28][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 2

HCID 9804-NitrophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

생성물 1

HCID 150678484-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 25.2%

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 10931941Silver imidazolate촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

A suspension of 5.6 g (15.8.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 2 g (14.3.10-3 mol) of 4-nitrophenol, 4 g (29.3.10-3 mol) of zinc chloride and 3.8 g (21.7.10-3 mol) of silver imidazolate in 80 ml of anhydrous methylene chloride is stirred at 50° C., under an inert atmosphere, in the absence of light and in the presence of a molecular sieve (400 pm). After 48 h at this temperature, the reaction mixture is filtered on Celite®, washed with a 1N aqueous solution of hydrochloric acid, then a 1N solution of sodium hydroxide and finally water and dried over magnesium sulfate (MgSO4). After evaporation to dryness, the residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 1.5 g (yield: 25%) of the expected product are obtained by precipitation in ether.

후처리

  1. filtrationthe reaction mixture is filtered on Celite®
  2. washwashed with a 1N aqueous solution of hydrochloric acid
  3. dry with materiala 1N solution of sodium hydroxide and finally water and dried over magnesium sulfate (MgSO4)
  4. customAfter evaporation to dryness
  5. customthe residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

출처 및 근거

ORD 기록
ord-5708f7344ec44077ac4ebc76cd2e78dd
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05101048

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